Perry Street Software is the kind of place that reminds you why “toxic workplace” became a cliché. The CEO is a money-driven robot with the emotional range of a wet paper towel — obsessed with numbers, indifferent to people, and incapable of genuine leadership. The COO operates like an unstable sideshow act: everyone walks on eggshells because his ego is made of glass, and one wrong word sends him spiraling into a tantrum that derails entire teams. It’s exhausting.
The culture? Utter chaos. Endless gossip, cliques, and whisper campaigns. Professionalism is nonexistent; it’s all politics and damage control. They hired a supposed “Product leader” who could’ve written a masterclass on grift — tanked the entire org, then somehow convinced leadership it was everyone else’s fault. The last PM standing behaves like a career parasite — manipulative, self-preserving, and allergic to accountability.
The company loves to shout about supporting the queer community, but don’t buy the PR sparkle. Behind the slogans, it’s performative allyship at best. The lack of women and people of color is glaring, and the company’s response to serious behavior issues has been, at times, shockingly indifferent.
People quit constantly. Firings happen suddenly, without clarity or compassion. HR spins it as “realignment” or “restructuring,” but everyone knows it’s dysfunction in disguise.
If you value integrity, emotional safety, or basic decency in leadership, do yourself a favor and look elsewhere. This place will drain you dry and leave you questioning your career choices.
In short: Perry Street Software is a cautionary tale wrapped in a rainbow logo. Stay. Far. Away.
